Rooting is as anyone will say, a risky business.
But the benefits may outweigh the risks.

1) Free Wi-Fi tethering2) Awesome backup applications that back up most files (some like Titanium even back up the SD card) to the Google data cloud.
3) The use of ROMS (Modified/enhanced/fully customizable alters to an OS, see CyanogenMod, ClockworkMod, etc) that give you full control and enhance the abilities of your Droid.4) A small (but fun/useful) feature is the ability to take screenshots on your device.5) The ability to clear your data cache from your device. For people with the flashed version of 2.3.3 (v. 4.5.588) who lost the bootloader menu, this is a godsend.

The biggest thing is it voids your warranty. If you plan on rooting, look around these forums for a while to find a simple, stable, and highly supported root.
I myself run a Droid X 2.3.3 (v 4.5.588) with Gingerbreak 1.2.
I love the abilities unlocked by root.